Sodium Formate → HCID 86642308, compound

HRID 905993Notes

Reaction equation

HRID 905993 reaction equation
[CH2:1]([NH:4][C:5]1[C:10](Br)=[N:9][C:8]([Br:12])=[CH:7][N:6]=1)[CH:2]=[CH2:3].C([O-])=O.[Na+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:12][C:8]1[N:9]=[C:10]2[C:2]([CH3:3])=[CH:1][NH:4][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723810Sodium FormateHCID 86642307HCID 86642307, compound

Product 1

HCID 86642308HCID 86642308, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of allyl-(3,5-dibromo-pyrazin-2-yl)-amine (3.51 g, 12.0 mmol), TEA (4 mL, 28.8 mmol), sodium formate (204 mg, 3.00 mmol), Bu4NH4Br (580 mg, 1.80 mmol), and Pd(OAc)2 (269 mg, 1.20 mmol) in 24 mL of DMF was heated at 50° C. overnight then cooled to RT. The reaction mixture was partitioned between EtOAc and brine. The organic layer was dried (MgSO4), concentrated, and purified by SiO2 chromatography (120 g SiO2, hexanes/EtOAc 0-70% EtOAc) to give 0.279 g of 2-bromo-7-methyl-5H-pyrrolo[2,3-b]pyrazine (11% yield).

Workup

  1. temperaturethen cooled to RT
  2. customThe reaction mixture was partitioned between EtOAc and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (120 g SiO2, hexanes/EtOAc 0-70% EtOAc)

Sources & evidence

ORD record
ord-7c8ebd6c141746a7bef219e230228d6b
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

Loading…